CA2546506C - Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables - Google Patents

Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables Download PDF

Info

Publication number
CA2546506C
CA2546506C CA2546506A CA2546506A CA2546506C CA 2546506 C CA2546506 C CA 2546506C CA 2546506 A CA2546506 A CA 2546506A CA 2546506 A CA2546506 A CA 2546506A CA 2546506 C CA2546506 C CA 2546506C
Authority
CA
Canada
Prior art keywords
formula
dba
process according
reaction
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2546506A
Other languages
English (en)
French (fr)
Other versions
CA2546506A1 (fr
Inventor
Thierry Dubuffet
Pascal Langlois
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratoires Servier SAS
Original Assignee
Laboratoires Servier SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratoires Servier SAS filed Critical Laboratoires Servier SAS
Publication of CA2546506A1 publication Critical patent/CA2546506A1/fr
Application granted granted Critical
Publication of CA2546506C publication Critical patent/CA2546506C/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06008Dipeptides with the first amino acid being neutral
    • C07K5/06017Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/72Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2546506A 2003-11-19 2004-11-18 Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables Expired - Fee Related CA2546506C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03292864A EP1420028B1 (fr) 2003-11-19 2003-11-19 Pocédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP03292864.0 2003-11-19
PCT/FR2004/002936 WO2005054276A1 (fr) 2003-11-19 2004-11-18 Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables

Publications (2)

Publication Number Publication Date
CA2546506A1 CA2546506A1 (fr) 2005-06-16
CA2546506C true CA2546506C (fr) 2010-04-06

Family

ID=32116380

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2546506A Expired - Fee Related CA2546506C (fr) 2003-11-19 2004-11-18 Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables

Country Status (29)

Country Link
US (1) US7208607B1 (ru)
EP (1) EP1420028B1 (ru)
JP (1) JP4377412B2 (ru)
KR (1) KR100863394B1 (ru)
CN (1) CN100447152C (ru)
AR (1) AR047312A1 (ru)
AT (1) ATE354586T1 (ru)
AU (1) AU2004295132B2 (ru)
BR (1) BRPI0416746B1 (ru)
CA (1) CA2546506C (ru)
CY (1) CY1106544T1 (ru)
DE (1) DE60311942T2 (ru)
DK (1) DK1420028T3 (ru)
EA (1) EA010102B1 (ru)
EG (1) EG26629A (ru)
ES (1) ES2282586T3 (ru)
GE (1) GEP20084547B (ru)
HK (1) HK1096689A1 (ru)
MA (1) MA28144A1 (ru)
MX (1) MXPA06005607A (ru)
MY (1) MY138550A (ru)
NO (1) NO336349B1 (ru)
NZ (1) NZ546931A (ru)
PL (1) PL210769B1 (ru)
PT (1) PT1420028E (ru)
SI (1) SI1420028T1 (ru)
UA (1) UA83269C2 (ru)
WO (1) WO2005054276A1 (ru)
ZA (1) ZA200603675B (ru)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE310012T1 (de) * 2003-08-29 2005-12-15 Servier Lab Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salzen
CZ2006427A3 (cs) 2003-12-29 2006-11-15 Sepracor Inc. Pyrrolové a pyrazolové inhibitory DAAO
CA2957667A1 (en) 2005-07-06 2007-01-11 Sepracor Inc. Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders
AU2006335174B2 (en) 2006-01-06 2012-09-06 Sunovion Pharmaceuticals Inc. Tetralone-based monoamine reuptake inhibitors
AU2007205114B2 (en) 2006-01-06 2012-11-08 Sunovion Pharmaceuticals Inc. Cycloalkylamines as monoamine reuptake inhibitors
AU2007233041B2 (en) 2006-03-31 2013-05-02 Sepracor Inc. Preparation of chiral amides and amines
US7884124B2 (en) 2006-06-30 2011-02-08 Sepracor Inc. Fluoro-substituted inhibitors of D-amino acid oxidase
US7902252B2 (en) 2007-01-18 2011-03-08 Sepracor, Inc. Inhibitors of D-amino acid oxidase
EP3296289A3 (en) 2007-05-31 2018-06-20 Sunovion Pharmaceuticals Inc. Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors
WO2016178591A2 (en) 2015-05-05 2016-11-10 Gene Predit, Sa Genetic markers and treatment of male obesity
FR3050380B1 (fr) 2016-04-20 2020-07-10 Les Laboratoires Servier Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains.
CN112047869B (zh) * 2020-08-20 2021-12-21 华南理工大学 一种氮杂5,6-并环化合物的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2620709B1 (fr) * 1987-09-17 1990-09-07 Adir Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese

Also Published As

Publication number Publication date
CY1106544T1 (el) 2012-01-25
US7208607B1 (en) 2007-04-24
DK1420028T3 (da) 2007-06-18
BRPI0416746A (pt) 2007-01-16
WO2005054276A1 (fr) 2005-06-16
SI1420028T1 (sl) 2007-06-30
EA010102B1 (ru) 2008-06-30
PT1420028E (pt) 2007-05-31
EP1420028A2 (fr) 2004-05-19
EG26629A (en) 2014-04-13
DE60311942D1 (de) 2007-04-05
EP1420028A3 (fr) 2004-05-26
ZA200603675B (en) 2007-09-26
EA200600898A1 (ru) 2006-10-27
CN1882607A (zh) 2006-12-20
JP2008502587A (ja) 2008-01-31
MY138550A (en) 2009-06-30
EP1420028B1 (fr) 2007-02-21
HK1096689A1 (en) 2007-06-08
MXPA06005607A (es) 2006-08-17
MA28144A1 (fr) 2006-09-01
US20070083052A1 (en) 2007-04-12
PL210769B1 (pl) 2012-02-29
AU2004295132B2 (en) 2010-07-15
DE60311942T2 (de) 2007-12-06
NZ546931A (en) 2010-01-29
CN100447152C (zh) 2008-12-31
BRPI0416746B1 (pt) 2018-02-14
UA83269C2 (ru) 2008-06-25
PL380409A1 (pl) 2007-01-22
AU2004295132A1 (en) 2005-06-16
CA2546506A1 (fr) 2005-06-16
JP4377412B2 (ja) 2009-12-02
NO336349B1 (no) 2015-08-03
NO20062599L (no) 2006-06-06
KR100863394B1 (ko) 2008-10-14
ATE354586T1 (de) 2007-03-15
AR047312A1 (es) 2006-01-18
GEP20084547B (en) 2008-11-25
KR20060121202A (ko) 2006-11-28
ES2282586T3 (es) 2007-10-16

Similar Documents

Publication Publication Date Title
CA2546506C (fr) Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables
EP1362864B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP1367061B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP0309324A1 (fr) Procédé de synthèse d'alpha amino N alkyles et de leurs esters. Application à la synthèse de carboxyalkyl dipeptides
EP1371659B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP1380590B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP1380591B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP1420029B1 (fr) Procédé de synthèse du perindopril et ses sels pharmaceutiquement acceptables
US6225480B1 (en) Sulphonyl compounds for use as linkers in solid phase and combinatorial synthesis
EP1422236B1 (fr) Procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
EP1367063B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
JP4279871B2 (ja) (2s,3as,7as)−1−[(s)−アラニル]−オクタヒドロ−1h−インドール−2−カルボン酸誘導体類を合成する新規な方法およびペリンドプリル合成におけるその使用
EP1367062B1 (fr) Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
KR20090007610A (ko) Ace-억제제의 합성에서의 약학적 중간체 및 이의 용도

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20191118